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Absolute Asymmetric Synthesis: Viedma Ripening of Co(bpy)(3) (2+) and Solvent-Free Oxidation to Co(bpy)(3) (3+)

Journal article
Authors Per Martin Björemark
Johan Jönsson
Mikael Håkansson
Published in Chemistry-a European Journal
Volume 21
Issue 30
Pages 10630-33
ISSN 0947-6539
Publication year 2015
Published at Department of Chemistry and Molecular Biology
Pages 10630-33
Language en
Links dx.doi.org/10.1002/chem.201500876
Keywords asymmetric synthesis, circular dichroism, cobalt, deracemization, structure elucidation, ATTRITION-ENHANCED DERACEMIZATION, CHIRAL-SYMMETRY-BREAKING, SOLID-STATE, CIRCULAR-DICHROISM, METAL-COMPLEXES, RESOLUTION, CRYSTALLIZATION, AUTOCATALYSIS, REAGENTS, 1,10-PHENANTHROLINE, Chemistry, Multidisciplinary
Subject categories Chemical Sciences

Abstract

Syntheses of [Co(bpy)(3)](2+) yield racemic solutions because the - and -enantiomers are stereochemically labile. However, crystallization and attrition-enhanced deracemization can give homochiral crystal batches of either handedness in quantitative yield. Subsequently, solvent-free oxidation with bromine vapour fixes the chirality because [Co(bipy)(3)](3+) does not enantiomerize in solution at ambient temperature. This combination of Viedma ripening and the labile/inert Co-II/Co-III couple constitutes a convenient method of absolute asymmetric synthesis.

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